S$ 468 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 23-9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Best Singapore Flight Deals from Chicago

Cheapest return prices found by our users on KAYAK in the last 72 hours
Singapore
Singapore1 stopS$ 908
Singapore
Singapore1 stopS$ 908

Cheap Flights from Chicago to Singapore

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Singapore

Wed, 10 Sep - Wed, 17 Sep
Air India Logo
12:00 - 07:30ORD-SIN
30h 30m1 stop
Air India Logo
20:30 - 07:25SIN-ORD
23h 55m1 stop
S$ 908Air India
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Mon, 15 Sep - Wed, 15 Oct
Air India Logo
12:00 - 21:45ORD-SIN
44h 45m1 stop
Air India Logo
09:00 - 07:25SIN-ORD
35h 25m1 stop
S$ 945Air India
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Tue, 7 Oct - Mon, 27 Oct
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
Cathay Pacific Logo
01:25 - 14:00SIN-ORD
25h 35m1 stop
S$ 1,080Cathay Pacific
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Mon, 15 Sep - Tue, 14 Oct
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
Cathay Pacific Logo
01:50 - 14:25SIN-ORD
25h 35m1 stop
S$ 1,083Cathay Pacific
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Sat, 30 Aug - Sun, 7 Sep
Air Canada Logo
20:08 - 07:05ORD-SIN
45h 57m2 stops
Air Canada Logo
09:10 - 08:01SIN-ORD
35h 51m2 stops
S$ 1,116Air Canada
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Tue, 7 Oct - Tue, 28 Oct
Air Canada Logo
15:35 - 07:05ORD-SIN
26h 30m1 stop
Air Canada Logo
10:00 - 07:58SIN-ORD
34h 58m2 stops
S$ 1,124Air Canada
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Tue, 19 Aug - Thu, 28 Aug
Logo
12:15 - 07:15ORD-SIN
30h 00m1 stop
Logo
01:55 - 21:03SIN-ORD
32h 08m2 stops
S$ 1,161
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Wed, 10 Sep - Wed, 17 Sep
Logo
23:45 - 17:20ORD-SIN
28h 35m2 stops
Logo
21:50 - 09:05SIN-ORD
24h 15m1 stop
S$ 1,183
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Wed, 16 Jul - Thu, 31 Jul
Japan Airlines Logo
01:30 - 17:30ORD-SIN
27h 00m1 stop
Japan Airlines Logo
08:05 - 23:43SIN-ORD
28h 38m2 stops
S$ 1,252Japan Airlines
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Wed, 23 Jul - Wed, 6 Aug
Japan Airlines Logo
01:30 - 17:30ORD-SIN
27h 00m1 stop
Japan Airlines Logo
01:55 - 23:59SIN-ORD
35h 04m2 stops
S$ 1,290Japan Airlines
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KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly, and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is February, when tickets cost S$ 1,123 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of return tickets is S$ 2,214 and S$ 1,837 respectively.

What’s the cheapest day of the week to fly from Chicago to Singapore?

The average price of all round-trip flights from Chicago to Singapore clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Singapore, you should consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on the flight from Chicago to Singapore, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

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Good to know

Low seasonAugust
High seasonDecember
Cheapest flightS$ 468
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly (50% more expensive on average)
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Singapore with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Singapore?

    The cheapest time of day to fly to Singapore is generally in the evening, when retur flights cost S$ 1,799 on average. Morning departures are around 28% more expensive than evening flights, on average. The most expensive time of day to fly to Singapore is generally in the morning, which is peak travel time and where the average cost of a ticket is S$ 2,310.

Top airline flying from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
Turkish AirlinesOverall score based on 3849 reviews
7.3Food
7.3Boarding
7.7Crew
7.4Entertainment
7.3Comfort
Airline reviews

I’ve been traveling for 20 years. I tried Turkish airline for the first time horrible horrible service and it would be my last time even if I get offer for a free ticket, I will not accept it. They have races and the worst Flight attendant

2.0 MediocreAnonymous, May 2025IAD - IST
Read more Turkish Airlines reviews

I’ve been traveling for 20 years. I tried Turkish airline for the first time horrible horrible service and it would be my last time even if I get offer for a free ticket, I will not accept it. They have races and the worst Flight attendant

It wasn't good. I didn’t understand. They changed 320 dollars for 2 luggage. My ticket was regular and I paid almost 1200.00 dollars. Why they did charge? I want my money back.. thanks Yılmaz polat

Very punctual, the onboard staff was friendly and correct, the flight was fortunately very calm, the toilets were clean, in short, an excellent experience Thanks

Ordered Vegan meal - it was ok, but not exceptional. Seat ok row 39 middle section aisle. Nearly full flight - crew was busy but they did the best they could. There was a USB A port at the seat. I listened to my own music and only looked at flight information. One nice thing was the connection information was made available in the screen.

Very nice and friendly crew. Boarding system can be improved.

The Etickets had been changed (Why?) without notice ; Hence, that caused troubles when checking in. Not until I contacted my ticket agent and was given correct Etickets could I then check in.

Cleanliness of seats, trays, storage pockets need more attention, but everything else was good.

A great airline, no complaints at all. My experience with Cheap Tickets was very disappointing however. Two hours after purchasing the flight they called to tell me that the ticket price had gone up. I’ve never heard of such a thing. That is called false advertising; I will never use this ticketing service again and will warn all friends to never use it.

One of the worst check in process at the DIA as well as the boarding counter Changed seat at the last minute and assigned middle seat while I paid for window seat. Requested many times but to no avail . horrible customer service and very poor process Requesting refund for seat that was changed last minute

Good overall flight. Excellent crew. Food options could be improved.

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights from Chicago to Singapore
Business Class flights from Chicago to Singapore
Prem Econ Class flights from Chicago to Singapore
Economy class flights from Chicago to Singapore

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